8 Rare Gems from Heidi Roizen on Building a Fulfilling Life and Career

Heidi Roizen is one of those names in Silicon Valley that everyone learns at some point. That’s what happens when you spend 14 years running your own company, then building developer relationships as a VP for Apple. Today, she’s an investor with DFJ Venture and teaches a class called the Spirit of Entrepreneurship at Stanford’s School of Engineering. Generally speaking, she’s someone who knows everyone (there’s even a Harvard Business School case about her) — and she’s wielded that influence gracefully.

Before graduation this year, she returned to Stanford (where she was also an undergraduate and business student), to speak at the Entrepreneurship Corner and share the lessons she has learned from over three decades of working and operating in tech. The result is a type of commencement speech for entrepreneurs, full of seldom shared gems based on her experiences.

Below are eight tenets Roizen has used to guide her career, create an expansive and lasting network, and shape new innovations. The beauty is that while they were delivered to an audience of people just starting out, they remain deeply relevant as a roadmap and important reminders for entrepreneurs at all stages.

1. If you’re not doing something hard, you’re wasting your time.Melinda Gates was once walking by her young daughter’s room, and watched as she tried to put on her shoes. “This is hard,” her daughter said. “But I like hard.” “I love that line,” says Roizen. “When you’ve been through a lot of hard things, you know that the best times are when you get through them.”

Successful entrepreneurs are constantly chasing a state of flow. “You know that feeling when you’re working right at the edge of your capability and you’re so engaged in trying and failing and trying more that time just flies? That’s when you’re really testing yourself. Ask yourself every day, every week, ‘What is something hard that I can tackle?’” It’s funny, Roizen says, that so many ambitious people still strive to eliminate difficulty from their careers — they want to cruise by, or land a dream job without earning it first — but that’s wrongheaded. “The reality is, when you get there, if you do, you’ll be bored. So look for the hard stuff.”

“The great thing about being an entrepreneur is that it's hard. There's no safety net. No regular paycheck. You have to do it all on your own.”

2. Your ethics set the tone for your life.When Roizen was CEO of her first company, T/Maker, there was a sprinkler malfunction that ruined all of the inventory in the stock room. Fortunately, it was mostly worthless. Even more fortunately (in another sense), their landlord didn’t know that and offered to cover any amount of damages with insurance. “It was really tempting — we could have collected $150,000 when we were bootstrapped,” she says. “But we decided to tell the truth, because not only did we know the inventory wasn’t worth anything, but our employees knew too. If we were willing to cheat, what would that tell them?”

When you’re setting an example for a staff of people, you have to be cognizant of every move that you make. If T/Maker’s leadership had taken the money, they would have sent the message that cheating is okay. “It would be the same as saying, 'Hey file an expense report that’s not true. Take home that extra piece of equipment if you want.'” Seems obvious, but it can be an incredibly hard lesson to learn, Roizen says. “You will think, 'I can take this easy road. I can say this thing. I can tell this customer something that isn’t really true about our product to make a sale.'”

“Sometimes you get away with it. Sometimes you don't. A lot of times you won't.”

“What you decide to do sets the tone and culture for the whole company you are building,” she says. “Part of this is being able to sleep at night. More of it is about being a good contributor to the people you work with and the relationships you build. This is easier when you hold yourself to a higher standard.”

3. Your gut has more information than you do.While in business school at Stanford, Roizen took a class called Creativity in Business that asked students to conduct an exercise for a week: Write down a decision you need to make the next day on a piece of paper, go to sleep, wake up in the morning and immediately make the decision. The purpose was to show students how gut decisions get made, and how right they can be.

Increasingly, tech culture is about the opposite — making decisions driven by exhaustive data. “There’s this idea that the more data you have, the better the decision you can make. That may be true for some things, but not everything,” says Roizen. “Gut instincts are built on years of experience and subconsciously what you observe about human nature from every interaction. They are informed in ways we don’t even understand.” She’s learned this several times the hard way, especially when it came to decisions about people — who to work with, who to keep on, who to fire. “When the data said something else and I didn’t go with my gut, I regretted it," she says.

4. Picking your team is the most important thing you will ever do.

“The vast majority of companies succeed or die by the quality of the team.”

Over the years, Roizen has seen a lot of young entrepreneurs make the same mistake. They have an idea for a company, they start their own thing, and when it comes time to hire executives, they don’t want to bring on anyone who knows more than them. “They don’t want to be intimidated, so they hire someone who is the same age and knows about the same stuff. You hire people who are familiar to you because you trust them.” This sounds good, but at the same time, you’re missing out on all kinds of expertise because you’re worried about being outgunned or sidelined.

“If you want to be the smartest person in the room, you're going to build a crummy team.”

“Do you really want a VP of sales who knows less about sales than you? Do you want a CFO who knows less about accounting? No of course not,” she says. “You have to take risks to find the right people and then trust in those relationships. Your job becomes to empower those people and make sure they get along. My goal is always to be the dumbest person in the room because I want to be surrounded by really bright, really amazing people. That’s when exciting, world-changing things get done.”

5. The art of negotiation is finding the optimal intersection of mutual need.In another one of Roizen’s business school classes, the students were paired off into buyers and sellers and told to negotiate the purchase of a car. Everyone had the same data, yet the difference between the highest sale price and the lowest at the end of class was drastic. She was shocked, and it shaped her perception of how negotiations work. As she puts it, when you first learn about transactions, you see them as a zero-sum game. You either want to make the most money you can, or pay the least. You don’t care who is on the other side of the deal. You want to win at their expense.

“I don’t believe anything in life is a transaction like this anymore,” Roizen says. “I believe everything is about relationships. If you have a transactional view of life, you think, ‘I’m not going to worry about the future. I’m going to worry about getting as much as I can right now.’ The relationship-based view is very different.”

“Nothing in life is a zero-sum game.”

“If I can walk into a transaction with you, and my goal is not to just make myself better off but to make you better off as well, we’re going to end up with a much better outcome. You’ll want to do business with me again — and that’s really, really important.”

Roizen has spent nearly her entire life in Silicon Valley, and has run into the same people again and again. This familiarity has only been compounded by Facebook profiles and Etsy ratings, and all kinds of other permanent metrics. “You are now the sum total of your transactions because they are relationships,” she says. “Every time you meet someone, think about the relationship instead of the transaction. If you know more about them and they know more about you, you will be able to collaboratively help each other.”

6. Life is actually really, really random.“Bad things will happen to you. You will fail. Things outside of your control will happen. You need to lean into this fact.” In this environment, how can you survive, much less strive for success? Roizen has one piece of advice: Expect things to be messy.

“The key to happiness is to lower your expectations.”

This doesn't mean you shouldn't go after your goals. It means you should prepare for an imperfect path on the way. For example, when Roizen travels internationally, she assumes her checked baggage will be lost, that her flight will be late, that the rental car won't be there waiting. “I assume everything that can go wrong will go wrong so when it actually happens, I’m not stressed,” she says. “I have a change of clothes in my carry-on; I schedule no meetings within two hours of landing; I expect the mess, and if it doesn’t happen, I’m pleasantly surprised. 95% of stress is self-inflicted.”

Roizen remembers one entrepreneur she knew in particular who would always make meticulous plans — everything would have to fall perfectly into place for things to work out, and of course they never did. “If you assume everything is going to go perfectly, bad things will happen to you. You will run out of money before you reach the next milestone. Accept that life will get messy, and when it does, pick yourself up again.”

“If you fall down and refuse to get up, you will be down the rest of your life.”

Remember, the other side of the randomness coin is that some really great things can and do happen. When they do, don’t balk at the opportunity. There’s no knowing what could happen. If you get three truly excellent job offers, don’t drive yourself nuts over picking the right one, for example. “The fact is if you pick one that’s bad and it goes out of business and you get fired, it may still be the greatest thing that ever happens to you. You might learn something amazing that you may not have learned sitting at that other safer job.”

A while ago, Roizen came across a book that said when people were asked about the best and worst things that happened to them in the last five years, most people said the same thing — even things like getting divorced, getting cancer, losing a job. “It’s shocking when you ask real people what has moved their life in the most positive directions, it is often those types of things. Sometimes bad things can be good when you allow randomness in your life.”

7. Get good at using your time.

“The most important thing you have is time because you can't make more of it.”

“You can do things to leverage your time with money and help, but at the end of the day, you’re going to run out of it, so you have to be really sensitive about how you spend it,” Roizen says. “A lot of people are really bad at understanding how much time things take. They have 1,000 unanswered emails and they say, ‘I have no idea how to handle this.’ Well, the solution is to not schedule more than five hours of things in a day to leave three hours to answer email and calls and read, and stay informed. When people say they don’t have time to do that, I say, ‘Of course you do. You just have to do them instead of other things.’”

Her advice: Think about every use of your time and give it all equal weight to start. Recognize that grunt work takes time. Reading takes time. Figure out what you like doing, what extends your capabilities the most, and organize your time to strike the right balance. Ideally, this leaves some space for reflection and sleep, but Roizen knows this isn’t always realistic.

“I was once an entrepreneur, and I did not live a balanced life,” she says. “I think we live our lives in a serial fashion — there are periods where you won’t have time to do everything you want. If you’re really excited about something, you can run on that for a while.” That's okay, as long as you're aware of the tradeoffs, she says. More time spent working means less time with family and friends. “There’s this fantasy that important things like relationships and communication don’t take any time to maintain, but they do.” You may not be perfectly balanced, but the key is to keep trying.

“If you don't give yourself space, there won't be any room for good, random things to happen to you.”

8. The 20-40-60 Rule.Espoused by actress Shirley MacLaine, the rule goes something like this: “At 20, you are constantly worrying about what other people think of you. At 40 you wake up and say, 'I’m not going to give a damn what other people think anymore.' And at 60 you realize no one is thinking about you at all.” The most important piece of information there, Roizen says: “Nobody is thinking about you from the very beginning.”

Of course, this is good news and bad news. The bad news is that no one is constantly wondering if you're okay, how much money you’re making, whether you’re fulfilled in your job or your relationships.

“You need to be your own advocate,” Roizen says. “If you’re in a job you don’t like, you need to be the one to change it. You can’t sit in your office and wait for someone to bring you the answer.”

“Your boss is not thinking about you. Your peers are not thinking about you. You need to think about you.”

Harsh. But there’s a flipside. People waste hours and hours torturing themselves over what other people think about them — and they do it needlessly. Even Roizen used to fret about showing up to meetings after long flights with the wrong shoes, or a wrinkled suit. “I would be so worried about what people were going to think if I couldn’t pull myself together. But then it occurred to me, I have never once been in a meeting where halfway through I thought, ‘Even though this person is smart, they have a wrinkle in their jacket, so they must not be very good.’ No one ever thinks that way.”

People have enormous capacity to beat themselves up over the smallest foibles — saying the wrong thing in a meeting, introducing someone using the wrong name. Weeks can be lost, important relationships avoided, productivity wasted, all because we’re afraid others are judging us. “If you find this happening to you, remember, no one is thinking about you as hard as you are thinking about yourself. So don’t let it all worry you so much.”